There is nothing wrong with dressing up like a ninja and strolling around your local community asking for candy on Halloween. You will have a lot of fun and will probably come home with a healthy (bad choice of words) sack of goods. But, for those of you out there who take this annual event more seriously I'm here to give my advice.
There are three areas to focus on when trying to get the highest return on your Trick or Treating
a) Costume: There is nothing you can do about your age, height or weight, so whatever you've got lets work with it. Your main goal here is to gain as many cuteness points as possible. This is to distract the home owner while you steal their goodies. Some may try for the more revealing outfits and others try for the more detailed costumes, but I recommend going for cuteness. Adorable animals always work to get the "honey, look at how adorable this kangaroo is here!" while you fill up your sack/roo-pouch hand over fist with Reese's Pieces.
b) Location: Greenwich has several areas fantastic for the professional trick or treater (North Mianus, Cos Cob, Old Greenwich, Riverside, Glenville, Byram, and on), but nothing beats the Maher Avenue corridor. This street has gained a reputation for being extremely charitable with its sugar distribution. Situated to the west of Maple Avenue and the east of the Greenwich Hospital, Maher offers just the right mix of wealthy homeowners, flat streets, wide sidewalks, and density of houses for an adorable pony to fill up her sack with snickers bars.
c) Time: I am not the first to identify Maher as a gold mine for the sweet tooth, so there will definitely be competition. For this reason it is wise to consider the time of your tour. If you go early you will be guaranteed candy at each house, but since the homeowners are aware of the pending flood of people they will be less lenient to let their patrons take a full handful. Maher homeowners are professional and understand the concept of rationing well. If you go too late there is a good chance of missing the boat and arriving at dry homes. It is very rare for a Maher house to have extra candy come November. I recommend starting off to the west (say Park Ave) as the sun starts to go down (Sunset tonight is at 5:52pm) and then landing on Maher a bit after 6pm. Once you have conquered this street (some aggressive T or Ters will bring multiple outfits to attack the same house - not recommended) there are many wonderful avenues to test your luck at to the west (Northfield, Williams, Perryridge).
Good luck to all the goblins, cowgirls, Lady Gagas and princesses out there. I wish you a fruitful (bad choice of words) evening.